Azasugar inhibitors of glycosidases and related enzymes are the subject of intense current interest. Polyhydroxylated piperidines and their synthetic analogues have attracted a great deal of attention in recent years due to their ability to mimic sugars, and competitively and selectively inhibit glycosidases and glycosyltransferases, the carbohydrate processing enzymes. These attributes make hydroxylated piperidines (azasugars) likely therapeutic agents for the treatment of diseases related to metabolic disorders involving carbohydrates such as diabetes, cancer, AIDS, and viral infections, where glycoprotein processing is crucial.
Delta-substituted α,β-unsaturated gamma-lactams are found among natural products, and they are useful as building blocks for the synthesis of a variety of biologically active compounds. Due to their conformational rigidity, reactions at the double bond, notably cycloadditions and conjugate additions, proceed with a high degree of stereocontrol.
US 2011/0263874 A1 discloses method of processing an initial compound having a formula (A)
Wherein R1 comprises a saturated or unsaturated, branched or un-branched group containing from 1 to 10 carbon atoms, and Wherein Z and X independently comprise one or more of C, H, O, N, S, a halide, and a counter-ion, the method comprising: converting the initial compound to a cyclic compound having a formula (B)
the converting comprising one or both of thermal and catalytic processing, the cyclic compound being present in a mixture comprising one or more additional components; and performing a purification to remove at least some of the one or more additional components.
U.S. Pat. No. 5,326,880 discloses asymmetrical polyvinyl pyrrolidonyl compounds and their uses as complexing and dispersing agents. Included two asymmetrical molecules, 1-methyl-3,6-dioxa-1,8-dipyrrolidonyl octane, which has two ether linkages, and N-ethylpyrrolidonyl-pyrrolidonylpolyoxypropylene, which has two or three ether linkages.
U.S. Pat. No. 6,559,150 B2 discloses that amide can be alkylated by deprotonation with a strong base such as sodium hydride, LHMDS, or KHMDS in a suitable solvent such as DMF or THF followed by treatment with an alkylating agent such as an alkyl halide, mesylate or tosylate.
U.S. Pat. No. 5,994,562 discloses a process for preparing N-alkenylcarbox amides by dehydration of N-(2-hydroxyalkyl)carboxamides and/or diethers. Dehydration of HEP with undoped catalysts yielded bis-N-etylpyrrolidone ether as an unwanted side product at concentrations up to 71%. WO 2015170339 A1 discloses a method of synthesis of piperidine alkaloids selected from fagomine, 4-epi-fagomine and nojirimycin from tri-O-benzyl-D-glucal or tri-O-benzyl-D-galactal.
US 2011/0263874 A1l/U.S. Pat. No. 8,501,963 B2 disclose the compound of formula as mentioned in the claim having no substitution in the piperidine rings at other positions. It basically involves cyclization of succinic acid derivatives to succinamide derivatives and further N alkylated pyrrolidinone derivatives using ammonia and then alkylating agent.
But, the present invention does not use ammonia and the starting material is cyclic compound (derived from carbohydrate) and by varying the conditions it gives different products as evident from scheme 1.
U.S. Pat. No. 5,326,880 disclose the compound of formula as mentioned in the claim which has no substitution on the pyrrolidone/piperidone rings at other positions, only polypyrrolidonyl compounds are synthesized from butyrolactone and substituted amine derivatives.
But, the present invention does not use butyrolactone and by varying the conditions it gives different product as shown in scheme 1. Instead the starting material is from carbohydrate.
U.S. Pat. No. 6,559,150 B2 discloses that amide can be alkylated by deprotonation with a strong base such as sodium hydride, LHMDS, or KHMDS in a suitable solvent such as DMF or THF followed by treatment with an alkylating agent such as an alkyl halide, mesylate or tosylate.
But, the present invention provides process in which varying the concentration of base not only gives the alkylated product but also an elimination product viz. α,β-unsaturated amides are formed, as shown in scheme 1.
U.S. Pat. No. 5,994,562 discloses a process for preparing N-alkenylcarbox amides by dehydration of N-(2-hydroxyalkyl)carboxamides and/or diethers. Dehydration of HEP with undoped catalysts yielded bis-N-etylpyrrolidone ether as an unwanted side product at concentrations up to 71%.
This has no correlation with the present invention wherein our process is non-catalytic for the synthesis of N-alkylpiperidine alkaloids.
There exists a commercial and industrial need for materials that exhibit excellent solvency and solvent compatibility/miscibility that also provide an improved safety profile. These are the objectives of the present invention, and to describe these lactam compounds, their compositions and uses thereof.